I think a bigger Hobie would be better. The H20 will do fine (if you want to go sailing together) but two H16's will be the most ideal. It will also help enhance your skills since you would be sailing on your own.

Its been a while but we cam across a good deal on a Hobie 16 and decided to throw down. being as big as we are I was questioning my purchase, but we have had a blast on it so far. On the lake with winds for sailing about 8-16mph, we get across the lake in a hurry and spend most of our time tacking. it came with a trap set but with the exception of the unexpected gust we haven't needed it yet. what we have learned is with our size it forces us to perfect our balancing and weight placement.

I Do have my cousin up every once in a while and he is about 140lb and the boat does run a little fast

Going ok! We are learning gradually. Season is almost over though. Still we plan on sailing through winter if we can. We had 28 boats on the start line last race day which was really good. We are very lucky to have a fleet like this so close by.

I sail my H-18 with close to 500# (combined skipper and crew weight) fairly often - no worries whatsoever with an H-18. Candidly, If it's blowing at a level you would typically want to be sailing in - say, 10 plus - someone with your experience likely wouldn't even notice the extra weight. I've also had a hell of a lot of fun with 500+ on a H16 but it was blowing pretty good and you had to be super careful not to burry the leeward bow (make no mistake, there's a significant difference in hull buoyancy between the 16 and 18!)

If the two of you are deadset on sharing a boat, my suggestion would be to go big (18, Tiger, 20, or 21). Otherwise I echo what others have suggested about going with two Hobie 16s. There's just so damn many 16s out there and the boat is still in production.